SU956444A1 - Process for producing resorcinol - Google Patents

Description

The use of the method according to the invention permits the process of obtaining resorcin to be eliminated due to exclusion from the technologist and (c) the chain of the sulfonation stage and neutralization of the acidic reaction products.

Example b In a steel autoclave with a capacity of 300 ml, 20 g (0.12 along) of 2,6-dichlorophenol (model compound), 80 g of a 75% aqueous solution of caustic potash, and 2 g of iron powder are placed. The autoclave is closed, heated to 200 ° C and maintained at this temperature for 60 minutes (pressure 10 atm). After cooling, the reaction mixture was diluted with 100 ml of water, iron powder was filtered off, and the solution was neutralized with concentrated hydrochloric acid. The resulting solution is filtered, extracted with n-butanol (4x300 ml). Butanol is distilled off, the residue is dissolved in boiling toluene and filtered from the resin, toluene is distilled off and 9.0 g (68%) of dark brown mass is obtained. .In the distillation of this mass, 5.3 g (40%) of the desired product are obtained.

Found,%: C 65.3; H 5-8. Mol weight. 110.

SbNbOg.

Calculated,%: C 65.5; H 5.5. Mol weight- 110.

Example 2. In a steel autoclave with a capacity of 300 ml, 30 g (0.18. Mol) of 2,6-dichlorophenol (a model compound), 120 g of a 70% aqueous solution of caustic potash, and 3 g of loroshko.raz iron are placed. The autoclave is closed, heated to 200 ° C and sh der l; and in ayut at this temperature for 60 minutes (pressure 10 atm). After treatment of the reaction mixture as described in example 1, 13.2 g (65%) of a dark brown mass are obtained, during distillation of which 8.3 g (42%) of resorcinol are obtained, t. Kip. FROM - AND 6 ° C / 2 mm Hg. Art.

Example 3. In a steel autoclave with a capacity of 300 ml load 40 g (0.24 mol) of 2,6-dichlorophenol (model compound), 160 g of a 75% aqueous solution of sodium hydroxide and 3 g of powdered iron obtained from experiment 1. Autoclave close, heated to 240 ° C and maintained at this temperature for 30 minutes (pressure 15 atm).

After treatment of the reaction mixture as described in, 16.6 g (63%) of crude resorcinol are obtained. Distillation of this mass yields 11.9 g (45%) of resorcinol, i.e. bale. 110 -113 ° C / 2 MiM of mercury Art., t. pl. 110 ° C.

Example 4. In a steel autoclave with a capacity of 300 ml, 40 g (0.24 mol) of a bottoms tail is obtained. According to GLC, 91.7% of 2,6-dichlorophenol, 5.6% of 2,4-dichlorophenol, 2, 7% 2,4,6-trichlorophenol, 4 g of powdered iron, 160 g of a 75% aqueous solution of caustic potash.

The autoslav is closed, heated to 200 ° C and maintained at this temperature of 60 MI (pressure 10 atm). After treating the reaction mixture as described in Example 1, 20.5 g (76%) of a dark brown mass are obtained, from which at B: aqum. 11.9 g (45%) of the desired product are obtained by distillation.

Paydeno,%: C 65.4; P 5.7. Mol

weight. BY.

SbNbOz.

Calculated,%: C 65.5; H 5.5. Mol weight. 110.

Example 5 (comparative). In a steel autoclave with a capacity of 300 ml, 20 g (0.12 mol) of 2,6-dichlorophenol (model compound), 80 g of a 75% aqueous solution of potassium hydroxide, 2 g of iron powder are placed. The autoclave is closed, heated

up to 160 ° C and maintained at this. Perurat 60 min (pressure 6 atm). After cooling the autoclave, the reaction mixture is diluted with 100 ml of water, the iron powder is filtered, the solution is neutralized with concentrated hydrochloric acid and extracted with n-butanol (4 x 300 ml). Butanol is distilled off and J 5 g of crystalline mass is obtained, m.p. 65 ° C. The physicochemical constants of the resulting product co: are embedded in the constants and the starting compound.

Example 6 (comparative). In a steel autoclave with a capacity of 300 ml, 20 g (0.12 mol) of 2,6-dichlorophenol (model compound), 80 g of a 75% aqueous solution of sodium hydroxide and 2 g of powdered iron are placed. The autoclave is closed, heated to 180 ° C and maintained at this temperature for 120 minutes (pressure 10 atm).

After cooling the autoclave, the reaction mixture is diluted with 100 ml of water, iron powder is filtered off, the solution is neutralized with concentrated hydrochloric acid and extracted with ether.

The ether is distilled off and 14 g of mass is obtained, which was found according to GLC from 60% of 2,6 dichlorophenol and 40% of β-resorcinol. By distilling this mass, 8 g of 2,6-dichlorophenol and 3 g (23%) of resorcinol are obtained.

Example7 (comparative). In a steel autoclave with a capacity of 1000 ml, 90 g (0.55 MOL) of 2,6-D of iichlorophenol (model compound), 540 g of a 50% aqueous solution of caustic potash, and 5 g of iron powder are loaded. The autoclave is closed, heated to 200 ° C and maintained at this temperature for 30 minutes (pressure 10 atm.). After cooling the autoclave, the reaction mixture is diluted with 500 ml of water,

iron powder is filtered off, the solution is neutralized with concentrated hydrochloric acid and extracted with butanol (6X500 ml). Butanol is distilled off, the residue is dissolved in hot toluene, after the distillation of which 20.1 g (33%) are obtained.

Claims (2)

The method of producing resorcinol by alkaline hydrolysis of benzene derivatives at elevated temperature, characterized in that, in order to simplify the process, chlorophenoxyacetic acid wastes containing a mixture of dichlorophenols and the hydrolysis process are carried out using 70-75% new aqueous alkali solution at a temperature of 200-240 ° C, a pressure of 10-20 atm in the presence of metallic iron as a catalyst. Sources of information taken into account during the examination: 1. Japanese application No. 52-87126, cl. 16C4.11, published. 07/20/77. 2. B. E. Berkman. Sulfonation and alkaline melting in the organic synthesis industry. M., Goskhimizdat, 1960, p. 95-106 (prototype).